Chemoselective Oxidative Esterification and Iodocyclization of Hydroxyalkynyl Aldehydes
Abstract We have described the chemoselective behavior of iodine in the oxidative esterification and electrophilic iodocyclization of hydroxyalkynyl aldehydes that contain a primary alcohol moiety. In the presence of an alcohol, which serves as the nucleophile and solvent, the reaction of the hydroxyalkynyl aldehydes and I2 proceeds through a hemiacetal species to give alkyl 4‐(3‐hydroxyalkynyl)benzoate esters. In CH2 Cl2, these substrates undergo an electrophilic iodocyclization through a cyclic iodonium ion to provide a synthetic route for the formation of the bioactive dihydrofuran/pyran ring system..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2017 |
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| Erschienen: |
2017 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:6 |
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| Enthalten in: |
Asian Journal of Organic Chemistry - 6(2017), 12, Seite 1893-1902 |
| Beteiligte Personen: |
Kumar, Shiv [VerfasserIn] |
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| Anmerkungen: |
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Umfang: |
10 |
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| doi: |
10.1002/ajoc.201700375 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Abstract We have described the chemoselective behavior of iodine in the oxidative esterification and electrophilic iodocyclization of hydroxyalkynyl aldehydes that contain a primary alcohol moiety. In the presence of an alcohol, which serves as the nucleophile and solvent, the reaction of the hydroxyalkynyl aldehydes and I2 proceeds through a hemiacetal species to give alkyl 4‐(3‐hydroxyalkynyl)benzoate esters. In CH2 Cl2, these substrates undergo an electrophilic iodocyclization through a cyclic iodonium ion to provide a synthetic route for the formation of the bioactive dihydrofuran/pyran ring system. | ||
| 700 | 1 | |a Patel, Monika |4 aut | |
| 700 | 1 | |a Saunthwal, Rakesh K. |4 aut | |
| 700 | 1 | |a Verma, Akhilesh K. |4 aut | |
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